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Jerkass Woobie: Grace Wexler. She's a stuck-up, self-centered bigot who shamelessly favors one daughter over the other, but later we learn that her family disowned her when she married Jake, who is Jewish. It's implied that she has some degree of self-hatred for being upset by the loss of her family, because she really and truly loves Jake. Once we figure this out, her trying to micro-manage Angela's life makes more sense. Grace sacrificed a lot to marry outside her religion, and she thinks if Angela does everything "just right" she'll never have to face the pain and pressure she did.
The Woobie: Aspiring writer/chessplayer and dutiful son Theo Theodorakis, whose primary duties are to his parents' business and his ill younger brother. His infatuation with Angela goes unrequited, and he later becomes a suspect in the Westing House bombings after accidentally blowing up his high school chemistry lab.
Angela, too. She spends the book dealing with her mother making a huge fuss out of the upcoming wedding, which Angela doesn't even want to do. She doesn't seem to have many friends and her bridal shower is full of women she doesn't even know. And she feels she can't just call off the wedding because she doesn't want to hurt her fiance or let her mother down.
Sun Lin Hoo. She spends the first part of the book completely homesick and unable to speak any English at all. It's implied that this is the case because no one speaks to her besides her husband.
Crow. Her mother died in childbirth and she was raised by her single father, but it's implied they weren't that close. She suffered from alcoholism, married at sixteen and never graduated from high school, and her actions led to her daughter's suicide-something she's never forgiven herself for.
Her daughter, Violet, doesn't fare much better. Her father wanted her to inherit his business, but she didn't, so he pretty much ignored her. She wasn't allowed to play with other children, being more or less isolated in her home. Her mother arranged a marriage for her with a crooked politician after forcing her apart from her true love, driving her to suicide.
Subverted with Chris Theodorakis. He has all the makings of one: Ill Boy in a wheelchair, doted on by his family, barely able to communicate with others. But he's consistently excited and cheerful throughout the game, making him too upbeat to be a proper woobie.
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